Abstract
The title compound, C25H25N3O, comprises a 2-amino-pyridine ring fused with a cyclo-heptane ring, which adopts a chair conformation. The central pyridine ring (r.m.s. deviation = 0.013 Å) carries three substituents, viz. a benzyl-amino group, a meth-oxy-phenyl ring and a carbo-nitrile group. The N atom of the carbo-nitrile group is significantly displaced [by 0.2247 (1) Å] from the plane of the pyridine ring, probably due to steric crowding involving the adjacent substituents. The phenyl and benzene rings are inclined to one another by 58.91 (7)° and to the pyridine ring by 76.68 (7) and 49.80 (6)°, respectively. In the crystal, inversion dimers linked by pairs of N-H⋯Nnitrile hydrogen bonds generate R 2 (2)(14) loops. The dimers are linked by C-H⋯π and slipped parallel π-π inter-actions [centroid-centroid distance = 3.6532 (3) Å] into a three-dimensional structure.
Highlights
The title compound, C25H25N3O, comprises a 2-aminopyridine ring fused with a cycloheptane ring, which adopts a chair conformation
Our interest in the preparation of pharmacologically active 3-cyanopyridines led us to synthesise the title compound and the X-ray crystal structure determination was undertaken in order to establish its conformation
The chair conformation of the cyclooctane ring and the planar conformation of the pyridine are similar to those found in the related structure 2-(4-bromo phenyl)-4-(4-methoxyphenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine (Çelik et al, 2013)
Summary
The pyridine nucleus is prevalent in numerous natural products and extremely important in the chemistry of biological systems (Bringmann et al, 2004). 3-Cyanopyridine or pyridine-3-carbonitrile derivatives attract particular attention for their wide-spectrum biological activity along with their importance and utility as intermediates in the preparation of a variety of heterocyclic compounds (Shishoo et al, 1983; Doe et al, 1990). 3-Cyanopyridines with different alkyl and aryl/. The pyridine nucleus is prevalent in numerous natural products and extremely important in the chemistry of biological systems (Bringmann et al, 2004). 3-Cyanopyridine or pyridine-3-carbonitrile derivatives attract particular attention for their wide-spectrum biological activity along with their importance and utility as intermediates in the preparation of a variety of heterocyclic compounds (Shishoo et al, 1983; Doe et al, 1990). Our interest in the preparation of pharmacologically active 3-cyanopyridines led us to synthesise the title compound and the X-ray crystal structure determination was undertaken in order to establish its conformation. The molecular structure of the title compound, showing the atom labelling.
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